Interaction of lignans with human sex hormone binding globulin (SHBG).
Lignans bind to sex hormone-binding globulin (SHBG). The lignan with the highest binding affinity is (+/-)-3,4-divanillyltetrahydrofuran. In a double Stobbe condensation--without use of protecting groups--a wide variety of lignans with different substitution pattern in the aromatic and aliphatic part of the molecule was synthesized. These lignans were tested in a SHBG-binding assay which allowed to deduce the following relationship between structure and activity: 1) (+/-)-diastereoisomers are more active than meso compounds 2.) the 4-hydroxy-3-methoxy (guajacyl) substitution pattern in the aromatic part is most effective 3.) the activity increases with the decline in polarity of the aliphatic part of the molecule.
Schöttner
M
M
Lehrstuhl Organische Chemie I, Universität Bayreuth, Germany.
Gansser
D
D
Spiteller
G
G
D001667:Binding, Competitive; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D006801:Humans; D007700:Kinetics; D017705:Lignans / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D008031:Lignin / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012738:Sex Hormone-Binding Globulin / Q000737:chemistry / Q000378:metabolism*; D013329:Structure-Activity Relationship
C110595:3,4-divanillyltetrahydrofuran; D005663:Furans; D017705:Lignans; D012738:Sex Hormone-Binding Globulin; D008031:Lignin